You are also putting multi-generational family savings into one investment. 

It will save you money, time, and headaches in the long run.

If the car you own is not necessary, you could save even more to sell your vehicle and move to a more economical car as this is a depreciating asset. 

Has this strategy worked for anyone to save time, money, and labor?

Roof size approx 2700sq feet- gaf woodland lifetime designer shingles (gives the slate look similar to what's on the house) - If I choose plain architectural shingles, I'll save 2k- TPO PVC flat roof over 10x30 extension- soffit & fascia repair and replace where necessary (some of the soffit wood has gotten rotten and would need to be replaced)- chose copper valley instead of aluminum (said I'll save $500 if going with aluminium)- plywood mostly in very good condition because of great original quality of the wood (said I'll probably only need 3 sheets replaced)- replace downspouts where necessary, maybe he'll replace 1-2- install cobra ridge vent

In this case, would it be wise to get an additional loan to cover the remainder of the property or wait until I am able to save up enough money on my own? 

Hello all, In the next few months in Denver area (highlands ranch) I am looking to sublease a 2 bed 2 bath apartment so we can move into a friends house and save a lot of cash instead.

The added interest you are saving, is also an illusion. 

They will cost more to establish due to the legal work required to create the structure, but will cost much less per year to operate, saving you money over the long term.

I don't have the money currently for another property but figured since the market is doing well right now, I would invest some money in stocks while I save up for the next.